Alkenes & Alkynes: Electrophilic Addition, Pericyclic reactions, Alkynyl anions

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Reactions + Reagents

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7 Terms

1
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RCH2=CH3 → RXCH=CH3

HX, +CR preferred for carbocation so X bonds on C next to R

<p>HX, +CR preferred for carbocation so X bonds on C next to R </p>
2
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RC≡CH → RCH3-CH=O

BH3 then H2O2, -OH

<p>BH<sub>3</sub> then H<sub>2</sub>O<sub>2</sub>, <sup>-</sup>OH</p>
3
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RCH=CH3 → RCH3-CH2OH

BH3 then H2O2, -OH

<p>BH<sub>3</sub> then H<sub>2</sub>O<sub>2</sub>, <sup>-</sup>OH</p>
4
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trans RHC=CHR → trans RH(HO)C-C(OH)HR

RCO3H then H2O/H+ or H2O/ -OH

<p>RCO<sub>3</sub>H then H<sub>2</sub>O/H<sup>+</sup> or H<sub>2</sub>O/ <sup>-</sup>OH</p>
5
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trans RHC=CHR → cis HR(HO)C=C(OH)RH

KMnO4, -OH/H2O low temp or OsO4/H2O

<p>KMnO<sub>4</sub>, <sup>-</sup>OH/H<sub>2</sub>O low temp or OsO<sub>4</sub>/H<sub>2</sub>O</p>
6
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RHC=CHR → RC(=O)H + C(=O)

  • OsO4, HIO4

or

  • O3, low temperature then Me2S (reducing agent)

<ul><li><p><strong>OsO<sub>4</sub>, HIO<sub>4</sub> </strong></p></li></ul><p>or </p><ul><li><p>O<sub>3</sub>, low temperature then Me2S (reducing agent)</p></li></ul><p></p>
7
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RC≡CH → RC≡C-Na+

NaNH2 (a base)

<p>NaNH<sub>2</sub> (a base)</p>